The great Paul Newman was so many things—actor, director, race car enthusiast, savvy businessman, generous humanitarian, devoted husband—that we occasionally forget about some of his other achievements. Namely: rocking navigator-style sunglasses so hard, we’re surprised the sun didn’t break at some point.

Stylish men have always had a special relationship with beautiful cars.

Probably because, if you think about it, they’re kind of the perfect accessory. Big, shiny, powerful—a little automotive affirmation can go a long way to securing your position in the Court of Cool. (We’re sure the King would agree.) But it’s not only those men defined by their cars who drive cool ones. And we’ve got the photo evidence to prove it.

Here’s a little history lesson for you: plain white T-shirts first appeared in the late 19th century, when some manufacturer decided to split the union suit into separates. And originally, they were meant to protect one’s finer outer layers from the perils of, well, sweat.

Like boxers for your chest.

But the rules have changed in the past century. The undershirt has, on occasion, been called to take sartorial center stage. Like before bed. Or between takes on set. Or during takes, for that matter. And throughout it all, some brave, overtly stylish men have succeeded in proving that these baser layers can be worth way more than their thread count.

Every Wednesday from here on out, we’re giving you a piece of our minds. Actually, more like five pieces. It’s a chance to get a deeper look into what makes the minds behind Kempt tick—you know, beyond the usual Internet handsomeness we’re serving up daily. So, welcome to our newest and most personal weekly feature: The Kempt Five.

The prospect of celebrating summer’s inaugural weekend might have you toying with the idea of spending the entire three days in a pair of shorts (especially if you plan on being poolside the whole time).

But going pantsless is a deceptively tricky move—wrought with pitfalls and misconceptions.

More often than not, they’re considered a necessary evil. Tom Ford famously said that a man should never wear them. Inevitably, someone will rib you with that moldy chestnut about never taking a man in shorts seriously. But in the right hands—er, on the right gams—they can be serviceable, arguably even stylish. It’s been done before, to varying degrees of success.

So, as menswear anthropologists, in our quest to find out how we got into this pantsless existential crisis, we present to you:

But we’ve also been known to bend the rules every so often, because... tequila. And today, we’re revising our stance once more to include the glorious celebration of a fabric that we rely on so dearly during the fall and winter months but won’t see much of for the next six or so. Like most of these holidays, the founding is dubious at best—but ultimately, it feels like a good enough reason to give the rugged wools a proper farewell until we meet again.

It’s just finally starting to warm up, but we’re not quite into gray cotton sweatshirt territory just yet...

Unless you’ve got one that’s been toughened up with a bit of merino wool, like this Dean Sweatshirt from Cardigan. At first glance, this heather-gray crewneck looks just like all the other upcycled cotton gym sweatshirts that have been flooding the market, but this one is secretly packing some extra warmth with a 50% merino wool/cotton blend. Here’s what else you need to know.

The Story: Cardigan is an NYC-based knitwear label focused solely on the concept of the sweater in all of its forms (most notably, the cardigan), so you can expect a thoughtfully made sweatshirt here—even down to the telltale triangle stitch at the collar.

Who to Channel: A young JFK sailing one of his first rigs; a particularly dapper boxer; Paul Newman on a dirt bike.

When to Wear It: When all signs point to a perfect spring day, but it’s actually still about 20 degrees colder than it looks.

The civil rights movement was born out of an ugly time in US history, but we’ll be damned if it didn’t make for some good-looking protesters.

With the always-impeccable Dr. Martin Luther King Jr. leading the way, a sea of crisp suits, skinny ties and Wayfarers led our country into equality. In honor of the great man and movement, we dug through the archives and were surprised to find a handsome lot of style icons also heading up the charge for civil rights—a veritable who’s who of impossibly cool gentlemen—everyone from Brando and Newman to Belafonte, Dylan and Davis Jr. Hell, even Charlton Heston got in on the action. It’s as if somehow impassioned, selfless endeavoring has a way of adding an extra layer of dapperness—not to mention being on the right side of history.

Warren Beatty on the phone as he campaigns for Senator George McGovern’s Democratic presidential nomination.

Leading up to his 1972 presidential bid, Senator George McGovern, who died over the weekend at the age of 90, met with a group of Hollywood celebrities at the home of Shirley MacLaine. Since he was not well-known and had little support within the Democratic Party, it was decided that the entertainment industry could lend the McGovern campaign some much-needed credibility, charisma and cash.

And so a new generation of Hollywood liberal activists emerged, the first to do so since McCarthyite blacklists of the early ’50s had driven showbiz liberalism deep into the walk-in closets of Malibu and Mulholland Drive.

Warren Beatty, MacLaine’s brother, scheduled a series of high-profile concerts, fundraisers and East Hampton pickup baseball games, attended by the likes of Jack Nicholson, Burt Lancaster, Dustin Hoffman, Jon Voight and so on. “We got involved because we were people who cared,” Norman Lear told The Hollywood Reporter on Sunday.

As such, we thought it a fitting tribute to the fallen senator to eulogize him in a pictorial we’re calling:

If you happen to be in Paris this month, drop by the Galerie Art District du Royal Monceau at the Royal Monceau–Raffles hotel, where you’ll find an exceptionally tasteful collection of celebrity photos from the ’60s and ’70s taken by Daniel Angeli, “father of the paparazzi.”

There’s a cerebral tone to Angeli’s shots, particularly when compared to the shit show of “gotcha” pics and videos littering newsstands and gossip sites these days. A code of sorts seems to be at play here—an invitation, rather than an interruption. Simply put, these are beautiful photographs of beautiful people in beautiful settings.

Take a look out your window. Chambray season is here. So we’d like to take this opportunity to give you a little visual inspiration on the subject—from Paul Newman, to what you’ll find in shops right now, to paratroopers in the South Pacific. But mostly for the excuse to make a Fifty Shades of Grey pun (even if we only made it about halfway to 50 pictures).